Organocatalyzed cyclopropanation of α-substituted α,β-unsaturated aldehydes: Enantioselective synthesis of cyclopropanes bearing a chiral quaternary center

Chemistry - A European Journal

Volumn 16, Issue 26, 2010, Pages 7875-7880

  Terrasson, Vincent ^a   Van Der Lee, Arie ^b   De Figueiredo, Renata Mareia ^a   Campagne, Jean Marc ^a  

^a INSTITUT CHARLES GERHARDT   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEX STRUCTURE; CYCLOPROPANATION; CYCLOPROPANE DERIVATIVE; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; GOOD YIELD; OPTICALLY ACTIVE; ORGANOCATALYTIC; QUATERNARY CARBON; QUATERNARY CENTERS; STEREOCENTERS; UNSATURATED ALDEHYDES;

BEARINGS (STRUCTURAL); ENANTIOSELECTIVITY; HYDROCARBONS; PROPANE;

ALDEHYDES;

EID: 77954340273     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000334     Document Type: Article

References (66)

1. For reviews on the creation, of quaternary carbon, stereocenters, see:
2. a) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402415;
3. Angew. Chem. Int. Ed. 1998, 37, 388-401;
4. b) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732;
5. Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
6. c)I, Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146;
7. d)D. J. Ramon, M. Yus, Curr. Org. Chem. 2004, 8, 149-183;
8. e)J. Christoffers, A. Baro, Quaternary StereocentersChallenges and Solutions for Organic Synthesis, Wiley-VCH, Weinheim, 2005;
9. f) J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473-1482;
10. g) B. M. Trost, C. Jiang, Synthesis 2006, 369-396;
11. h) P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969-5994.
12. Review on organocatalytic approaches for creation of quaternary carbon, stereocenters, see: M. Bella, T. Gasperi, Synthesis 2009, 1583-1614.
13. For excellent reviews on stereoselective cyclopropanation, see:
14. a) H. Pellissier, Tetrahedron 2008, 64, 7041-7095;
15. b) H. Lebel, J. F. Marcoux, C. Molinaro, A.B. Charette, Chem. Rev. 2003, 103, 977-1050 and references therein. For a recent highlight,
16. see: R. S. Goudreau, A. B. Charette, Angew. Chem. 2010, 122, 496-498;
17. Angew. Chem. Int. Ed. 2010, 49, 486-488.
18. For asymmetric organocatalyzed cyclopropanation by catalystbound ylides, see:
19. a) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482-1485;
20. Angew. Chem. Int. Ed. 2001, 40, 1433-1436;
21. b) C.D. Papageorgiou, M. A. Cubillo de Dios, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004, 116, 4741-4744;
22. Angew. Chem. Int. Ed. 2004, 43, 4641-4644. For enantioselective cyclopropanation upon olefin activation by indoline-2-carboxylic acid catalysts, see:
23. c)R. K. Kunz, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240-3241;
24. d)A. Hartikka, P.I. Arvidsson, J. Org. Chem. 2007, 72, 5874-5877;
25. e) A. Hartikka, A. T. Šlósarczyk, P. I. Arvidsson, Tetrahedron: Asymmetry 2007,18,1403-1409. For cinchona alkaloids as catalysts, see:
26. f) S. H. McCooey, T. McCabe, S. J. Connon, J. Org. Chem. 2006, 71, 7494-7497;
27. g) S. Kojima, M. Suzuki, A. Watanabe, K. Ohkata, Tetrahedron Lett. 2006, 47, 9061-9065;
28. h) C. C. C. Johansson, N. Bremeyer, S. V. Ley, D. R. Owen, S. C. Smith, M. J. Gaunt, Angew. Chem. 2006, 118, 6170-6175;
29. Angew. Chem. Int. Ed. 2006, 45, 6024-6028;
30. i)J. Lv, J. Zhang, Z. Lin, Y. Wang, Chem. Eur. J. 2009,15, 972-979.
31. For (±)proline as catalyst with bromonitroalkanes, see: J.-M. Zhang, Z.-P. Hu, S.-Q. Zhao, M. Yan, Tetrahedron 2009,65, 802-806.
32. For the first organocatalytic enantioselective cyclopropanations of αβ-unsaturated aldehydes with diphenylprolinol derivatives as catalyst, see:
33. a) R. Rios, H. Sunden, X Vesely, G.-L. Zhao, P. Dziedzic, A. Córdova, Adv. Synth. Catal. 2007, 349, 1028-1032;
34. b) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am Chem. Soc. 2007,129, 1088610894;
35. c)I. Ibrahem, G.-L. Zhao, R. Rios, J. Vesely, H. Sundén, P. Dziedzic, A. Córdova, Chem. Eur. J. 2008, 14, 7867-7879;
36. d)X. Companyó, A.-N. Alba, F. Cárdenas, A. Moyano, R. Rios, Eur. J. Org. Chem. 2009, 3075-3080. For a recent iminium/enamine cyclopropanation in aqueous medium, see:
37. e) U. Una, J. L. Vicario, D. Badía, L. Carrillo, E. Reyes, A. Pesquera, Synthesis 2010, 701-713.
38. For an example of enantioselective nitrocyclopropanation of α,β-unsaturated aldehydes a-cyanoimides by afunctional thiourea as catalyst, see: T. Inokuma, S. Sakamoto, Y. Takemoto, Synthesis 2009, 1627-1630.
39. For selected reviews, see:
40. a) J. Salaun, Chem. Rev. 1989, 89, 12471270;
41. b) A.-H. Li, L-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372;
42. c)A. Pfaltz in Comprehensive Asymmetric Catalysis (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, pp. 513-538;
43. d)R. Faust, Angew. Chem. 2001, 113, 2312-2314;
44. Angew. Chem. Int. Ed. 2001, 40, 2251-2253;
45. e) H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196;
46. f) C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009,38, 3051-3060.
47. 2Ph] was used to forge a quaternary stereocenter under enamine catalysis to the synthesis ofα,α-chlorofluoro carbonyl compounds, see: K. Shibatomi, H. Yamamoto, Angew. Chem. 2008, 720, 5880-5882;
48. Angew. Chem. Int. Ed. 2008, 47, 5796-5798.
49. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 8032-8034;
50. Angew. Chem. Int. Ed. 2009, 48,7892-7894.
51. a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005,117, 804-807;
52. Angew. Chem. Int. Ed. 2005, 44, 794-797;
53. b) M. Marigo, D. Fielenbach, A. Braunton, A. Kjasgærd, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769-3772;
54. Angew. Chem Int. Ed. 2005, 44, 3703-3706;
55. c)Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287;
56. Angew. Chem. Int. Ed. 2005, 44,4212-4215.
57. Our screening of the reaction solvent has been, started with EtOH based on Jørgensen and co-workers studies on the first organocatalytic enantioselective addition of malonates to aromatic α,β-unsaturated aldehydes: S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411-4415;
58. Angew. Chem. Int. Ed. 2006, 45,4305-4309.
59. This is particularly problematic using amine-promoted a-alkylation of aldehydes in the presence of alkylhalides. For an intramolecular a-alkylation of halo-aldehydes, see:
60. a) N. Vignola, B. List, J. Am. Chem. Soc. 2004,126, 450-451. For combination of organocatalysis and metal-catalysis by SOMO activation of aldehydes radical, see:
61. b) D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77-80. For excellent highlights on the a-alkylation of aldehydes, see:
62. c)P. Melchiorre, Angew. Chem. 2009,121,1386-1389;
63. Angew. Chem. Int. Ed. 2009, 48,1360-1363;
64. d)A.-N. Alba, M. Viciano, R. Rios, ChemCatChem 2009, 1,437-439.
65. a) X. Moreau, J. M. Campagne, J. Organomet. Chem. 2003, 687, 322-326;
66. b) Z. L. Tong, P. Gao, H. B. Deng, L. Zhang, P.-F. Xu, H. B. Zhai, Synlett 2008, 3239-3241.